Boron trifluoride etherate → 1-(5-Bromopyridin-2-yl)cyclopropanamine

HRID 589188Notes

Reaction equation

HRID 589188 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.B(F)(F)F.[CH3:14][CH2:15]OCC.C([Mg]Br)C.[Cl-].[NH4+]>C(O[Ti](OCCC)(OCCC)OCCC)CC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([NH2:9])[CH2:15][CH2:14]2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 25517Ammonium ChlorideHCID 8171545-Bromopyridine-2-carbonitrileHCID 178418443HCID 178418443, compound

Product 1

HCID 573568181-(5-Bromopyridin-2-yl)cyclopropanamine

Reagents, catalysts & solvents 1

HCID 178460667HCID 178460667, compoundCatalyst

Procedure

To a mixture of 5-bromopicolinonitrile (1.82 g, 10.0 mmol), tetrapropoxytitanium (3.26 ml, 11.0 mmol) and boron trifluoride diethyl etherate (2.51 ml 20.0 mmol) at 0° C. was added ethylmagnesium bromide (1.0M in ether, 22 ml, 22.0 mmol) The resulting solution was allowed to stir at it for 3 h. Ammonium chloride solution was added and the solution was extracted with ethyl acetate for three times. The organic layers were collected and washed with brine and dried over sodium sulfate. After concentration the crude product was purified by SiO2 column.

Workup

  1. extractionthe solution was extracted with ethyl acetate for three times
  2. customThe organic layers were collected
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationAfter concentration the crude product
  6. customwas purified by SiO2 column

Sources & evidence

ORD record
ord-5b023a48a0a84626ab80487d3c2adf35
Source dataset
uspto-grants-2016_01
Patent number
US09227971B2

Reaction notes

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